The Best Oscar Dresses of All Time: A History of Fashion at the Academy Awards

Joanne Woodward, herself, 1958

How much does it cost to get a dress for the Oscars? In Joanne Woodward’s case, $125 in fabric. Woodward, who won for her work in The Three Faces of Eve, made her green dress herself. Why did she decide to do that? She told the Associated Press that she didn’t think she would win. “So I didn’t want to invest too much,” she said. Paired with white gloves, it looked just as glamorous as anyone else’s gown. Later, she would say how happy she was with her creation. “Why, I’m almost as proud of the dress as I am the Oscar.”

Rita Moreno, designer unknown, 1962 and 2018

Every Academy Award for Best Supporting Actress

Rita Moreno's Oscar frock with a brocade skirt didn’t come from a famous designer. She wrote in her 2013 memoir that she took time off from shooting the movie Cry of Battle in The Philippines to attend the ceremony where she was nominated for supporting actress for West Side Story and ordered the dress made of Japanese obi fabric. That dress became iconic when Moreno became the first Latina actor to win an Academy Award. She wore it again 56 years later at the 2018 ceremony in what was maybe the ultimate Oscar dress flex.

Cher, Bob Mackie, 1986

Can you even call what Cher wore to the 1986 Oscars a dress? It’s a look. It’s an Oscars outfit. It’s an ensemble of the highest order. The over-the-top headpiece with the midriff-baring set was orchestrated out of revenge when Cher was not nominated for her work in Mask. Just two years later she would win best actress for her turn in Moonstruck in another Bob Mackie creation, but nothing will match the sheer absurdity of the 1986 getup.

Nicole Kidman, John Galliano, 1997

A Galliano masterpiece adorned Nicole Kidman when she accompanied her then husband Tom Cruise, who was nominated for Jerry Maguire. The chartreuse gown with a slit up the side and a floral design is now revered, but at the time, Joan Rivers yelled, “Nicole! Come tell me why you wore such an ugly color!”

Cate Blanchett, John Galliano, 1999

The Galliano Cate Blanchett wore, with flowers climbing up her back, is so stunning that it is now part of the collection of the Museum of Fine Arts in Boston. The optical illusion of the florals makes them appear as though they were growing out of her skin, while the front is appropriately slinky. Given that she was nominated for Elizabeth, she’s almost dressed down from her role but still striking even without a hoop skirt.

Björk, Marjan Pejoski, 2001

Does the swan belong on the list of best Academy Awards dresses of all time? In my mind, yes. The kitschy look is what the Icelandic singer Björk wore when she was nominated for best original song for her tragic composition “I’ve Seen It All” from Lars von Trier’s Dancer in the Dark. The dress was instantly mocked, even during the ceremony, but what few realize even now was that Björk was in on the gag. She said in response: “C’mon, you don’t bring eggs unless you want to take the piss, right?”

Julia Roberts, Valentino, 2001

Julia Roberts radiated simple elegance when she won best actress for her work in Erin Brokovich wearing this black-and-white Valentino piece. It was actually vintage at the time, originally from 1992, but she reinvented it as her own.

Halle Berry, Elie Saab, 2002

A historic night required one of the best Oscar dresses in the case of Halle Berry, who became the first Black performer to win best actress for her role in Monster’s Ball at the 2002 ceremony. “I saw so many gowns, but this one just felt the part: classic, couture, modern and sexy,” Berry told the Los Angeles Times.

Michelle Williams, Vera Wang, 2006

A personal favorite for many is Michelle Williams’s yellow Vera Wang gown, with a plunging neckline accentuated by a feathery bust. Williams was nominated for Brokeback Mountain that year, and the styling that accompanied the already excellent garment was spot on. Her bright red lips perfectly complemented the unusual saffron color.

Lupita Nyong'o, Prada, 2014

In the lead-up to Lupita Nyong’o’s best-supporting-actress win for 12 Years a Slave, the actress had gone from relative unknown to major celebrity and fashion maven. She capped it off with this baby blue—technically Nairobi blue—number from Prada with a flowing skirt. Was it the most beautiful Oscar dress of all time? Quite possibly.

Emma Stone, Givenchy, 2017

Sometimes stars dress like the trophies they are going to win. That was the case with Emma Stone when she took home her first Oscar for best actress in La La Land. She wore a stunning gold Givenchy gown with fringe. At the time, it was noted that she was the first lead actress to win an Oscar while wearing Givenchy since Audrey Hepburn. (Though whether Hepburn’s was actually Givenchy is a matter of opinion.)

Billy Porter, Christian Siriano, 2019

No need to leave Oscar fashion to the women. Billy Porter took our breath away when he showed up to the 2019 ceremony in this splendid Christian Siriano tux gown. It mashed up the best of menswear with the drama of a full skirt.

Natalie Portman, Dior, 2020

There are many ways in which Oscar fashion can make a statement. At the 2020 awards, Natalie Portman’s Dior cape did so literally. Portman’s outerwear was embroidered with the names of a number of female directors who were not nominated for best director, a reference to the fact that there was an all-male lineup that year. The filmmakers who got a shoutout included Greta Gerwig, Lorene Scafaria, Mati Diop, and Lulu Wang.

Lily Gladstone, Gucci and Joe and Sunshine Big Mountain, 2024

The best red-carpet gowns often mean something deeper. That was certainly the case when Lily Gladstone stepped out in a deep blue Gucci made alongside the Native American designers Joe and Sunshine Big Mountain. The collaboration demonstrated Gladstone’s commitment to elevating Indigenous designers, a responsibility she took on as the first woman of Native descent to be nominated for best actress. And what do you wear to an Academy Awards party? For the Vanity Fair Oscar Party, she changed into a beaded look by the same team.

Honorable Mentions